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(12) United States Patent (10) Patent No.: US 9,409,853 B2 Schuch Et Al

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(12) United States Patent (10) Patent No.: US 9,409,853 B2 Schuch Et Al USOO9409853B2 (12) United States Patent (10) Patent No.: US 9,409,853 B2 Schuch et al. (45) Date of Patent: Aug. 9, 2016 (54) POLYGLYCEROL PARTIAL ESTERS, 69/732 (2013.01); A61 K 2800/30 (2013.01); PREPARATION AND USE THEREOF A61 K 2800/49 (2013.01) (58) Field of Classification Search (71) Applicants: Dominik Schuch, Haan (DE); Wolfgang CPC ...... C07C 69/52; C07C 67/08; C07C 69/732; Berkels, Bottrop (DE); Oliver Springer, A61K 8/375; A61K 8/39; A61K 8/86; A61O Wesel (DE); Christian Hartung, Essen 1/14: A01O 5/02: A01O 15700; A01O 19/10 (DE); Hilke Condé, Gladbeck (DE): USPC .......................................................... 554/219 Baerbel Klann-Metz, Essen (DE) See application file for complete search history. (56) References Cited (72) Inventors: Dominik Schuch, Haan (DE); Wolfgang Berkels, Bottrop (DE); Oliver Springer, U.S. PATENT DOCUMENTS Wesel (DE); Christian Hartung, Essen 5,840,943 A 11/1998 Ansmann et al. (DE); Hilke Condé, Gladbeck (DE): 6,581,613 B2 6/2003 Berkels et al. Baerbel Klann-Metz, Essen (DE) 7,851,511 B2 12/2010 Allefet al. 7,906,664 B2 3/2011 Allefet al. 8,211,972 B2 7/2012 Meyer et al. (73) Assignee: EVONIK DEGUSSA GMBH, Essen 8,642,525 B2 2/2014 Herrwerth et al. (DE) 2013,0071340 A1 3/2013 Wenk et al. 2013/0171087 A1 7/2013 Herrwerth et al. (*) Notice: Subject to any disclaimer, the term of this 2013/0204021 A1 8/2013 Hartung et al. patent is extended or adjusted under 35 2013/0281552 A1 10/2013 Nilewski et al. U.S.C. 154(b) by 4 days. 2014f0072521 A1 3/2014 Meyer et al. (21) Appl. No.: 14/564,408 FOREIGN PATENT DOCUMENTS EP 1197.559 4/2002 (22) Filed: Dec. 9, 2014 EP 2273966 1, 2011 JP 2008119568 5, 2008 (65) Prior Publication Data WO WO2004O41769 5, 2004 WO WO2007027447 A1 3, 2007 US 2015/O315123 A1 Nov. 5, 2015 WO WO2009 1383.06 A1 11 2009 OTHER PUBLICATIONS (30) Foreign Application Priority Data Wilson, R., et al., “Overview of the Preparation, Use and Biological Dec. 5, 2013 (DE) ......................... 10 2013 224957 Studies on Polygycerol Polyricinoleate (PGPR)”. Food and Chemi cal Toxicology, Jan. 1998, p. 721, 36. European Search Report dated Apr. 23, 2015, received in a corre (51) Int. Cl. sponding foreign application. C07C 59/00 (2006.01) Schrader, K. et al., “Grundlagen and Rezepturen der Kosmetika' C07C 69/52 (2006.01) “Principles and Formulations of Cosmetics”, 1989, 2nd edition, p. C07C 67/08 (2006.01) 329 to 341, Hüthig BuchVerlag Heidelberg. A6 IK S/37 (2006.01) Cassel, S., et al., “Original Synthesis of Linear, Branched and Cyclic C07C 69/732 (2006.01) Oligoglycerol Standards'. European Journal of Organic Chemistry, A6 IK 8/39 (2006.01) Mar. 2001, vol. 2001, Issue 5, pp. 875-896. A61O I/14 (2006.01) Primary Examiner — Deborah D Carr A61O 5/02 (2006.01) (74) Attorney, Agent, or Firm — Scully, Scott, Murphy & A61O 15/00 (2006.01) Presser, P.C. A6 IK 8/86 (2006.01) (57) ABSTRACT A61O 19/10 (2006.01) (52) U.S. Cl. Polyglycerol partial esters of a specific composition which CPC ................. C07C 69/52 (2013.01); A61K 8/375 are capable of solubilizing very hydrophobic, oil-soluble sub (2013.01); A61K 8/39 (2013.01); A61K 8/86 stances in aqueous solution are provided. The preparation and (2013.01); A61O 1/14 (2013.01); A61O 5/02 use of these polyglycol ether-free solubilizers in cosmetic (2013.01); A61O 15/00 (2013.01); A61O 19/10 formulations are also disclosed. (2013.01); C07C 67/08 (2013.01); C07C 18 Claims, No Drawings US 9,409,853 B2 1. 2 POLYGLYCEROL PARTIAL ESTERS, long-chain triglycerides, in water or to solubilize a cosmetic PREPARATION AND USE THEREOF formulation, which is not possible using the products based on polyglycerol esters available to date. FIELD OF THE INVENTION A further advantage of the present invention is that the polyglycerol partial esters described herein may be prepared The present invention relates to polyglycerol partial esters exclusively from renewable raw materials in contrast to poly of a specific composition which are capable of Solubilizing ethoxylated triglycerides. very hydrophobic, oil-soluble Substances in aqueous solu A yet further advantage of the present invention is that the tion. The present invention also relates to the preparation and polyglycerol partial esters described herein are liquid, and use of these polyglycol ether-free solubilizers in cosmetic 10 thus readily processable, in contrast to polyethoxylated trig formulations. lycerides. An even further advantage of the present invention com PRIOR ART pared to the polyethoxylated triglycerides is that the polyg Non-ionic Surfactants having hardly any foam-generating 15 lyceryl esters described herein lead to particularly clear dis effect are usually employed as solubilizers of oil-soluble, persions of the oil in the water, and also no cloudiness occurs hydrophobic substances in water. on storage, in contrast to polyethoxylated triglycerides (PEG Polyethoxylated triglycerides, particularly based on castor 40 hydrogenated castor oil). oil, e.g., PEG-40 hydrogenated castor oil, are used as standard Another advantage of the present invention is that formu solubilizers. The latter is virtually able to clearly solubilize lations may be provided that are polyglycol ether-free. oil-soluble substances of a wide variety of structures and A further advantage of the polyglycerol partial esters hydrophobicity in water. Polyglycol ether-free polyglycerol described herein is that the polyglycerol partial esters of the partial esters have also been used for some years as alternative present invention can produce a pleasant skin sensation in solubilizers. cosmetic formulations. The disadvantage of all polyglycerol partial esters avail 25 Another advantage of the polyglycerol partial esters able to date is that their use as solubilizers of oil-soluble described herein is that the polyglycerol partial esters of the Substances in water cannot cover as wide a Substance spec present invention exhibit only a very low foam formation on trum as the previously mentioned polyethoxylated triglycer stirring in water. ides. The polyglycerol esters are thus mainly suitable for A further advantage is that the polyglycerol partial esters solubilizing 'small molecules such as, for example, short 30 described herein show only a very low effect on foamability chain terpenes. In contrast, oils based on fatty acids and and foam quantity in Surfactant formulations, but the foam triglycerides of long-chain fatty acids such as jojoba oil. creaminess can, however, improve. almond oil, soybean oil or avocado oil cannot, to date. be Another advantage is that the polyglycerol partial esters clearly solubilized in water using the commercial products described in the present invention may lead to attenuation of based on polyglycerol partial esters. 35 the skin irritancy in Surfactant formulations. JP 2008-119568 describes the use of polyglycerol partial A further advantage of the polyglycerol partial esters esters as solubilizers of oils in which the polyglycerol partial described herein is that the polyglycerol partial esters of the esters are based on mixtures of saturated fatty acids having 8 present invention can have a stabilizing effect in emulsions. to 22 carbonatoms and unsaturated fatty acids having 16 to 22 A further advantage of the inventive products is that they carbon atoms, wherein the molar ratio of Saturated to unsat 40 are relatively stable to oxidation and more stable with respect urated fatty acids is in a range of 0.2 to 0.8 to 0.8 to 0.2. In to color, odor and appearance. addition, polyglycerol partial esters of polyricinoleic acid may be admixed with this polyglycerol partial ester. DETAILED DESCRIPTION OF THE INVENTION SUMMARY OF THE INVENTION 45 The present invention provides polyglycerol partial esters of general formula I One object of the present invention is to provide solubiliz ers based on polyglycerol partial esters which, in contrast to the products available on the market to date, are able to clearly general formula I solubilize, in particular, hydrophobic, oil-soluble Substances, 50 Such as long-chain triglycerides, in water and to Solubilize RO O cosmetic formulations. It has been Surprisingly found that the polyglycerol partial OR2 esters described in the present invention are able to rectify the disadvantages of the prior art and thus enable to achieve the 55 where object of the present invention mentioned above. n=2 to 16, preferably 4 to 14, particularly preferably 5 to 11, In one embodiment of the present invention, polyglycerol R", R, R-independently of one another, identical or differ partial esters are provided which are prepared from polyglyc ent, selected from H. R. and erol by esterification of a specifically selected fatty acid mix R, where ture. The products are able to clearly solubilize very hydro 60 R=Saturated or unsaturated acyl residue having 6-22 carbon phobic, oil-soluble Substances, such as long-chain atoms, preferably 8-18 carbon atoms, comprising no triglycerides, in water or to solubilize a cosmetic formulation. hydroxyl groups, The preparation and use of these solubilizers in cosmetic R=Saturated or unsaturated acyl residue having 6-22 carbon formulations is also part of this invention. atoms, preferably 14-22 carbon atoms, comprising at least An advantage of the present invention is that the polyglyc 65 one hydroxyl group or an acyl residue of an oligomer of erol partial esters described herein are able to clearly solubi saturated or unsaturated acyl residues having 6-22 carbon lize strongly hydrophobic, oil-soluble Substances, such as atoms, preferably 14-22 carbon atoms, comprising at least US 9,409,853 B2 3 4 one hydroxyl group, in which the acyl residue of the oli noyland hydroxystearoyl residues, based on all R residues in gomer preferably has 26 to 66 carbon atoms, the polyglycerol partial ester, in which it is preferred that the characterized in that the molar ratio of the acyl residues R to mixture of ricinoyl and hydroxy Stearoyl residues has a molar R is in a range of 95.5 to 5:95, preferably 85:15 to 15:85, ratio of ricinoyl to hydroxystearoyl residues in a range of 100 particularly preferably 85:15 to 50:50.
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